Nearly all phosphoramides have been synthesized from phosphoryl chloride and amines. This reaction is adequate for academic research, but it is impractical for commercial production of oil-soluble products, because the water-washing step required for removal of chlorides causes severe emulsification problems.
Amine phosphate salts have been prepared by heating an amine and the corresponding O,O-dihydrocarbyl phosphoric acid. When trialkyl phosphates are reacted with amines, they act as alkylating agents with the product forming as illustrated below, where R and R.sup.1 are alkyl: EQU (RO).sub.3 PO + R.sup.1 NH.sub.2 .fwdarw. (RO).sub.2 PO.sub.2 NRR.sup.1 H.sub.2
this type of reaction is illustrated in U.S. Pat. No. 2,563,506.
When R in the above reaction sequence is aromatic, no reaction between the amine and the phosphate occurs.